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  Direct Asymmetric α-Hydroxylation of Cyclic α-Branched Ketones through Enol Catalysis

Shevchenko, G. A., Pupo, G., & List, B. (2019). Direct Asymmetric α-Hydroxylation of Cyclic α-Branched Ketones through Enol Catalysis. Synlett, 30(1), 49-53. doi:10.1055/s-0037-1611084.

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 Creators:
Shevchenko, Grigory A.1, Author           
Pupo, Gabriele1, Author           
List, Benjamin1, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: enol catalysis; α-hydroxy ketones; Brønsted acid catalysis; hydroxylation; chiral phosphoric acid
 Abstract: Enantiopure α-hydroxy carbonyl compounds are common scaffolds in natural products and pharmaceuticals. Although indirect approaches towards their synthesis are known, direct asymmetric methodologies are scarce. Herein, we report the first direct asymmetric α-hydroxylation of α-branched ketones through enol catalysis, enabling a facile access to valuable α-keto tertiary alcohols. The transformation, characterized by the use of nitrosobenzene as the oxidant and a new chiral phosphoric acid as the catalyst, delivers a good scope and excellent enantioselectivities.

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Language(s): eng - English
 Dates: 2018-09-072018-10-102018-11-142019-01-02
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1055/s-0037-1611084
 Degree: -

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Title: Synlett
  Other : Synlett
Source Genre: Journal
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Publ. Info: Stuttgart : Georg Thieme Verlag
Pages: - Volume / Issue: 30 (1) Sequence Number: - Start / End Page: 49 - 53 Identifier: ISSN: 0936-5214
CoNE: https://pure.mpg.de/cone/journals/resource/954925570856